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But he have a plethora of Dragon's at his side. Though, this leaves him with a huge weakness to Ice, he can easily counter this with Kingdra and, whoa, sweep her whole team with a single Dragon.
And really, in a battle between them, you guys really think he can't counter... Anything? Even a single non-STABed Ice type attack?
He's not diverse as Cynthia, but he does have some high chances to win. It's 50% chance for each one.
Also, Lance's a Specialist in Dragon Types. He knows how to play with both his Weakness and Advantages. Lets keep that in mind, people, he's not a simple "Dragon Trainer" with a Dragonite, Kingdra, Hydreingon, Garchomp, Salamence and Haxorus

Sure, huge-weakness to Ice; yet, he's a former champion. No chance at all? Not a single-damn-chance? Not a 1% of chance? By golly, you guys are mean!!

This is pretty much what I was going to say. Lance being a mono-type trainer makes it very easy for a trainer like Cynthia who doesn't specialize in one type to exploit his weaknesses.

Yes. Milotic and Garchomp on their own can sweep his whole team. Even if Lance and Cynthia had the same levels, OR EVEN IF LANCE HAD HIGHER LEVELS!
Even without Milotic or Garchomp cynthia can smash Lance.

When it come to the anime you can't be sure about anything. However logically speaking of course lance can win, I used his exact team minus altaria to beat Cynthia in the game any times for fun. My team was

Salamence
Charizard
Dragonite
Gyarados
Blastioise
Garchomp

Why do people automatically jump right on Cynthia's side? However, I do have to admit that the Pokemon writers do seemingly have a favorable few towards Cynthia. Lances Pokemon being weak to ice beam really matter that much to mean Cynthia will win for 100%? I highly doubt in the anime Cynthia will be using ice beam only and successfully hitting lance's Pokemon.

Lance has a seriously powerful team (Not that Cynthia doesn't). If I had to take a side I would pick lance. The match will be very very close. This is assuming the writer were thinking logically and not automatically predetermining that Cynthia will win because someone in their writing team fancies Cynthia.

I'm voting for Cynthia. She is really a beast c: (Well her Pokémon) and I guess every one else stated this already, she has more different pokémon, while lance's team is more mono typed. I don't think any of lance pokémon could actually out speed Cynthia's Garchomp.

There is no upperhand hand, I'm giving you mine. It doesn't have to end up wasting your time. There's things that I could say, here in my way. I wanna let you know, that it's all okay.

Cynthia definitely. She has balanced team and Lance is obviously bit dumb. His last pokemon would be Altaria and he would use Perish Song- LOL- Cynthia would switch and wait until Altaria faints. That way Lance has lost to me twice. He also uses Draco Meteor many times in a row wrecking his Dragonites special attack and then he uses Hyper Beam that is very weak after those Draco Meteors and takes 2 turns.

Recreate both rematch teams but make it fair by making all of the Pokemon the same level.

EDIT: I see people have done it on Youtube but most of the time it's just 1 person doing it so he can control everything that happens. One guy for instance spammed Dragon Dance with Gyrados and destroyed Cynthia.